Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2006 |
| Outros Autores: | , , , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/10445 |
Resumo: | Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, Brasil |
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Bernardino, Alice Maria RolimPinheiro, Luiz Carlos da SilvaRodrigues, Carlos RangelLoureiro, Natália IzabelCastro, Helena CarlaRangel, Adriana LanfrediLopes, Juliano SabatiniBorges, Júlio CésarCarvalho, Jane MariaRomeiro, Gilberto AlvesFerreira, Vitor FranciscoFrugulhetti, Izabel C. P. PSantos, Marcos André Vannier dos2015-05-20T18:54:34Z2015-05-20T18:54:34Z2006BERNARDINO, A. M. R. Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives. Bioorganic & Medicinal Chemistry, v. 14, n. 16, p. 5765-5770, 2006.0968-0896https://www.arca.fiocruz.br/handle/icict/1044510.1016/j.bmc.2006.03.013engElsevierDesign, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivativesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleUniversidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, BrasilUniversidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, BrasilUniversidade Federal do Rio de Janeiro. Faculdade de Farmácia. Rio de Janeiro, RJ, BrasilUniversidade Federal Fluminense. Instituto de Biologia. Departamento de Biologia Celular e Molecular. Niterói, RJ, BrasilUniversidade Federal Fluminense. Instituto de Biologia. Departamento de Biologia Celular e Molecular. Niterói, RJ, BrasilFundação Oswaldo Cruz. Centro de Pesquisa Gonçalo Moniz. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisa Gonçalo Moniz. Salvador, BA, BrasilUniversidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, BrasilUniversidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, BrasilUniversidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, BrasilUniversidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, BrasilUniversidade Federal Fluminense. Instituto de Biologia. Departamento de Biologia Celular e Molecular. Niterói, RJ, BrasilFundação Oswaldo Cruz. Centro de Pesquisa Gonçalo Moniz. Salvador, BA, BrasilIn this work, we performed the design, synthesis, and the structure–activity relationship studies of 13 new derivatives of thieno[2,3-b]pyridine. These derivatives were prepared in high yields (96–70%) and their structures were elucidated by IR, 1H, 13C NMR, and MS. The biological results showed some derivatives as antiparasitic agents against Giardia lamblia. Computational analysis of HOMO and LUMO energy, HOMO orbital coefficient distribution, electrostatic potential map, dipole moment, and density HOMO was performed to gain insight into the SAR aspects. This study pointed the p-methoxy substituted derivative as a leading compound for the development of new microbicidal medicines based on thieno[2,3-b]pyridine analogsAminopiridinasAntiprotozoáriosGiardia lambliaTiofenosinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82352https://www.arca.fiocruz.br/bitstream/icict/10445/1/license.txtafbdf7d7a9bcf771a1cc7edf5f618413MD51ORIGINALBernardino AMR Design, synthesis..........pdfBernardino AMR Design, synthesis..........pdfapplication/pdf268628https://www.arca.fiocruz.br/bitstream/icict/10445/2/Bernardino%20AMR%20Design%2c%20synthesis..........pdfbe03f8d00d370f83d4dd27b7b9c2da48MD52TEXTBernardino AMR Design, synthesis..........pdf.txtBernardino AMR Design, synthesis..........pdf.txtExtracted texttext/plain26046https://www.arca.fiocruz.br/bitstream/icict/10445/3/Bernardino%20AMR%20Design%2c%20synthesis..........pdf.txt3ff77d586c6e5a280e9273d48e9ddf60MD53icict/104452023-03-15 14:33:06.447oai:www.arca.fiocruz.br:icict/10445Q0VTU8ODTyBOw4NPLUVYQ0xVU0lWQSBERSBESVJFSVRPUyBBVVRPUkFJUwoKQW8gYWNlaXRhciBvcyBURVJNT1MgZSBDT05EScOHw5VFUyBkZXN0YSBDRVNTw4NPLCBvIEFVVE9SIGUvb3UgVElUVUxBUiBkZSBkaXJlaXRvcyBhdXRvcmFpcyBzb2JyZSBhIE9CUkEgZGUgcXVlIHRyYXRhIGVzdGUgZG9jdW1lbnRvOgoKQ0VERSBlIFRSQU5TRkVSRSwgdG90YWwgZSBncmF0dWl0YW1lbnRlLCDDoCBGSU9DUlVaIC0gRlVOREHDh8ODTyBPU1dBTERPIENSVVosIGVtIGNhcsOhdGVyIHBlcm1hbmVudGUsIGlycmV2b2fDoXZlbCBlIE7Dg08gRVhDTFVTSVZPLCAKdG9kb3Mgb3MgZGlyZWl0b3MgcGF0cmltb25pYWlzIE7Dg08gQ09NRVJDSUFJUyBkZSB1dGlsaXphw6fDo28gZGEgT0JSQSBhcnTDrXN0aWNhIGUvb3UgY2llbnTDrWZpY2EgaW5kaWNhZGEgYWNpbWEsIGluY2x1c2l2ZSBvcyBkaXJlaXRvcyAKZGUgdm96IGUgaW1hZ2VtIHZpbmN1bGFkb3Mgw6AgT0JSQSwgZHVyYW50ZSB0b2RvIG8gcHJhem8gZGUgZHVyYcOnw6NvIGRvcyBkaXJlaXRvcyBhdXRvcmFpcywgZW0gcXVhbHF1ZXIgaWRpb21hIGUgZW0gdG9kb3Mgb3MgcGHDrXNlczsKICAgICAgICAKQUNFSVRBIHF1ZSBhIGNlc3PDo28gdG90YWwgbsOjbyBleGNsdXNpdmEsIHBlcm1hbmVudGUgZSBpcnJldm9nw6F2ZWwgZG9zIGRpcmVpdG9zIGF1dG9yYWlzIHBhdHJpbW9uaWFpcyBuw6NvIGNvbWVyY2lhaXMgZGUgdXRpbGl6YcOnw6NvIApkZSBxdWUgdHJhdGEgZXN0ZSBkb2N1bWVudG8gaW5jbHVpLCBleGVtcGxpZmljYXRpdmFtZW50ZSwgb3MgZGlyZWl0b3MgZGUgZGlzcG9uaWJpbGl6YcOnw6NvIGUgY29tdW5pY2HDp8OjbyBww7pibGljYSBkYSBPQlJBLCBlbSBxdWFscXVlciAKbWVpbyBvdSB2ZcOtY3VsbywgaW5jbHVzaXZlIGVtIFJlcG9zaXTDs3Jpb3MgRGlnaXRhaXMsIGJlbSBjb21vIG9zIGRpcmVpdG9zIGRlIHJlcHJvZHXDp8OjbywgZXhpYmnDp8OjbywgZXhlY3XDp8OjbywgZGVjbGFtYcOnw6NvLCBleHBvc2nDp8OjbywgCmFycXVpdmFtZW50bywgaW5jbHVzw6NvIGVtIGJhbmNvIGRlIGRhZG9zLCBwcmVzZXJ2YcOnw6NvLCBkaWZ1c8OjbywgZGlzdHJpYnVpw6fDo28sIGRpdnVsZ2HDp8OjbywgZW1wcsOpc3RpbW8sIHRyYWR1w6fDo28sIGluY2x1c8OjbyBlbSBub3ZhcyAKb2JyYXMgb3UgY29sZXTDom5lYXMsIHJldXRpbGl6YcOnw6NvLCBlZGnDp8OjbywgcHJvZHXDp8OjbyBkZSBtYXRlcmlhbCBkaWTDoXRpY28gZSBjdXJzb3Mgb3UgcXVhbHF1ZXIgZm9ybWEgZGUgdXRpbGl6YcOnw6NvIG7Do28gY29tZXJjaWFsOwogICAgICAgIApSRUNPTkhFQ0UgcXVlIGEgY2Vzc8OjbyBhcXVpIGVzcGVjaWZpY2FkYSBjb25jZWRlIMOgIEZJT0NSVVogLSBGVU5EQcOHw4NPIE9TV0FMRE8gQ1JVWiBvIGRpcmVpdG8gZGUgYXV0b3JpemFyIHF1YWxxdWVyIHBlc3NvYSDigJMgZsOtc2ljYSAKb3UganVyw61kaWNhLCBww7pibGljYSBvdSBwcml2YWRhLCBuYWNpb25hbCBvdSBlc3RyYW5nZWlyYSDigJMgYSBhY2Vzc2FyIGUgdXRpbGl6YXIgYW1wbGFtZW50ZSBhIE9CUkEsIHNlbSBleGNsdXNpdmlkYWRlLCBwYXJhIHF1YWlzcXVlciAKZmluYWxpZGFkZXMgbsOjbyBjb21lcmNpYWlzOwogICAgICAgIApERUNMQVJBIHF1ZSBhIG9icmEgw6kgY3JpYcOnw6NvIG9yaWdpbmFsIGUgcXVlIMOpIG8gdGl0dWxhciBkb3MgZGlyZWl0b3MgYXF1aSBjZWRpZG9zIGUgYXV0b3JpemFkb3MsIHJlc3BvbnNhYmlsaXphbmRvLXNlIGludGVncmFsbWVudGUgCnBlbG8gY29udGXDumRvIGUgb3V0cm9zIGVsZW1lbnRvcyBxdWUgZmF6ZW0gcGFydGUgZGEgT0JSQSwgaW5jbHVzaXZlIG9zIGRpcmVpdG9zIGRlIHZveiBlIGltYWdlbSB2aW5jdWxhZG9zIMOgIE9CUkEsIG9icmlnYW5kby1zZSBhIAppbmRlbml6YXIgdGVyY2Vpcm9zIHBvciBkYW5vcywgYmVtIGNvbW8gaW5kZW5pemFyIGUgcmVzc2FyY2lyIGEgRklPQ1JVWiAtIEZVTkRBw4fDg08gT1NXQUxETyBDUlVaIGRlIGV2ZW50dWFpcyBkZXNwZXNhcyBxdWUgdmllcmVtIGEgCnN1cG9ydGFyLCBlbSByYXrDo28gZGUgcXVhbHF1ZXIgb2ZlbnNhIGEgZGlyZWl0b3MgYXV0b3JhaXMgb3UgZGlyZWl0b3MgZGUgdm96IG91IGltYWdlbSwgcHJpbmNpcGFsbWVudGUgbm8gcXVlIGRpeiByZXNwZWl0byBhIHBsw6FnaW8gCmUgdmlvbGHDp8O1ZXMgZGUgZGlyZWl0b3M7CiAgICAgICAgCkFGSVJNQSBxdWUgY29uaGVjZSBhIFBvbMOtdGljYSBJbnN0aXR1Y2lvbmFsIGRlIEFjZXNzbyBBYmVydG8gZGEgSW5zdGl0dWnDp8OjbyBlIGFzIGRpcmV0cml6ZXMgcGFyYSBvIGZ1bmNpb25hbWVudG8gZG8gcmVwb3NpdMOzcmlvIAppbnN0aXR1Y2lvbmFsIEFSQ0EKRepositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352023-03-15T17:33:06Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.pt_BR.fl_str_mv |
Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives |
| title |
Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives |
| spellingShingle |
Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives Bernardino, Alice Maria Rolim Aminopiridinas Antiprotozoários Giardia lamblia Tiofenos |
| title_short |
Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives |
| title_full |
Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives |
| title_fullStr |
Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives |
| title_full_unstemmed |
Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives |
| title_sort |
Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives |
| author |
Bernardino, Alice Maria Rolim |
| author_facet |
Bernardino, Alice Maria Rolim Pinheiro, Luiz Carlos da Silva Rodrigues, Carlos Rangel Loureiro, Natália Izabel Castro, Helena Carla Rangel, Adriana Lanfredi Lopes, Juliano Sabatini Borges, Júlio César Carvalho, Jane Maria Romeiro, Gilberto Alves Ferreira, Vitor Francisco Frugulhetti, Izabel C. P. P Santos, Marcos André Vannier dos |
| author_role |
author |
| author2 |
Pinheiro, Luiz Carlos da Silva Rodrigues, Carlos Rangel Loureiro, Natália Izabel Castro, Helena Carla Rangel, Adriana Lanfredi Lopes, Juliano Sabatini Borges, Júlio César Carvalho, Jane Maria Romeiro, Gilberto Alves Ferreira, Vitor Francisco Frugulhetti, Izabel C. P. P Santos, Marcos André Vannier dos |
| author2_role |
author author author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Bernardino, Alice Maria Rolim Pinheiro, Luiz Carlos da Silva Rodrigues, Carlos Rangel Loureiro, Natália Izabel Castro, Helena Carla Rangel, Adriana Lanfredi Lopes, Juliano Sabatini Borges, Júlio César Carvalho, Jane Maria Romeiro, Gilberto Alves Ferreira, Vitor Francisco Frugulhetti, Izabel C. P. P Santos, Marcos André Vannier dos |
| dc.subject.decs.pt_BR.fl_str_mv |
Aminopiridinas Antiprotozoários Giardia lamblia Tiofenos |
| topic |
Aminopiridinas Antiprotozoários Giardia lamblia Tiofenos |
| description |
Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, Brasil |
| publishDate |
2006 |
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2006 |
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2015-05-20T18:54:34Z |
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2015-05-20T18:54:34Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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BERNARDINO, A. M. R. Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives. Bioorganic & Medicinal Chemistry, v. 14, n. 16, p. 5765-5770, 2006. |
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https://www.arca.fiocruz.br/handle/icict/10445 |
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0968-0896 |
| dc.identifier.doi.none.fl_str_mv |
10.1016/j.bmc.2006.03.013 |
| identifier_str_mv |
BERNARDINO, A. M. R. Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives. Bioorganic & Medicinal Chemistry, v. 14, n. 16, p. 5765-5770, 2006. 0968-0896 10.1016/j.bmc.2006.03.013 |
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Elsevier |
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